Sodium hydride → HCID 131724706, compound

HRID 853097Notes

Reaction equation

HRID 853097 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[CH3:11])[NH:7][C:6]([CH:12]([C:17]([CH3:22])([CH3:21])[CH:18]([CH3:20])[CH3:19])[O:13][SiH:14]([CH3:16])[CH3:15])=[CH:5]2.[H-].[Na+].[C:25]([O:29][C:30]([N:32]1[CH2:36][C@H:35]([CH3:37])OS1(=O)=O)=[O:31])([CH3:28])([CH3:27])[CH3:26]>CN(C)C=O>[C:25]([O:29][C:30](=[O:31])[NH:32][CH2:36][C@H:35]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([Br:1])=[C:10]([CH3:11])[CH:9]=2)[CH:5]=[C:6]1[CH:12]([C:17]([CH3:21])([CH3:22])[CH:18]([CH3:19])[CH3:20])[O:13][SiH:14]([CH3:15])[CH3:16])[CH3:37])([CH3:28])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11195739(s)-Tert-butyl 5-methyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxideHCID 178422359HCID 178422359, compound

Product 1

HCID 131724706HCID 131724706, compoundYield 58.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.95 g 5-bromo-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-6-methyl-1H-indole in 10 ml N,N-dimethylformamide was added 0.143 g sodium hydride 55–65% in oil and the mixture was stirred 30 min at room temperature. To the resulting mixture was added (S)-5-methyl-2,2-dioxo-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester (0.703 g) and the mixture was stirred 2 h at room temperature. The reaction mixture was partitioned between water and ethyl acetate. The phases were separated and the organic phase was washed with 10% citric acid and brine, dried over magnesium sulfate and purified by chromatography on silica gel with hexane:ethyl acetate=5:1 to yield 0.789 g (R)-(2-{5-bromo-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-6-methyl-indol-1-yl}-propyl)-carbamic acid tert-butyl ester as a slightly yellow oil. ISP-MS: M+H=541.3

Workup

  1. stirringthe mixture was stirred 2 h at room temperature
  2. customThe reaction mixture was partitioned between water and ethyl acetate
  3. customThe phases were separated
  4. washthe organic phase was washed with 10% citric acid and brine
  5. dry with materialdried over magnesium sulfate
  6. custompurified by chromatography on silica gel with hexane

Sources & evidence

ORD record
ord-a856fda1beed46ee933ba8c41664817d
Source dataset
uspto-grants-2007_08
Patent number
US07253281B2

Reaction notes

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